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Piroxicam dose- and time-dependently induced gastric lesions in rats. The piroxicam-induced gastric lesions, both in acute (18-h) and in sub-chronic (3- and 14-day) treatments, were significantly inhibited by co-administration with the standard nitric oxide (NO) donor, S-nitrosoglutathione (GSNO). The extent of inhibition of lesion formation was dependent on the doses of both piroxicam and GSNO. GSNO affected neither the pharmacokinetics nor the pharmacological effect of piroxicam in the phenylbenzoquinone-induced writhing test. A new structural class of NSAIDs which contains a nitrosothiol moiety linked by a tether to a NSAID by an ester bond was synthesized. Ketoprofen-SNO (NMI-246) and ibuprofen-SNO (NMI-172) were designed to release NO in the gastrointestinal (GI) tract and liberate their respective parent NSAID. These SNO-NSAIDs were GI-sparing and equipotent to their respective parent NSAID in both the rat carrageenan-induced paw edema and phenylbenzoquinone-induced writhing tests. In conclusion, combination of NSAIDs with NO-donors or NSAID derivatives with a NO-donating moiety are effective GI-sparing antiinflammatory analgesics.